U.S. Ser. No. 273294 entitled "Lubricating Oil Succinimide Dispersants Derived from Heavy Polyamine", filed Jul. 11, 1994, discloses imidization of functionalized hydrocarbons or polymers with heavy polyamine and is incorporated by reference herein.
U.S. Ser. No. 261554 entitled "Lubricating Oil Dispersants Derived from Heavy Polyamine", filed Jun. 17, 1994, discloses amidation (derivatization) of polymers functionalized by the Koch reaction with heavy polyamine and is incorporated by reference herein.
U.S. Ser. No. 261507, entitled "Amidation of Ester Functionalized Hydrocarbon Polymers", filed Jun. 17, 1994, discloses a preferred amidation process for polymers functionalized by the Koch reaction and use of heavy polyamine therein and is incorporated by reference herein.
U.S. Ser. No. 322715 entitled, "Lubricating Oil Mannich Base Dispersants Derived from Heavy Polyamine" , filed Oct. 12, 1994, discloses an oil-soluble lubricating oil additive useful as a dispersant, comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with an aldehyde and a heavy polyamine and is incorporated by reference herein.
Mannich Base condensation products are used as dispersants in lubricating oil applications. They are typically prepared by reacting an alkyl substituted phenol, formaldehyde and a polyalkylene polyamine.
U.S. Pat. No. A-5017299 and the divisional thereof, U.S. Pat. No. A-5186851, disclose dispersants comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl moiety of the aromatic compound is derived from at least one ethylene alpha-olefin copolymer of 300 to 10,000 number average molecular weight, wherein at least about 30 percent of the polymer's chains contain terminal ethenylidene unsaturation, and are incorporated by reference herein.
U.S. Pat. No. A-3442808 discloses lubricating oil additives prepared by reacting an alkenyl succinic anhydride with a Mannich condensation product prepared by condensing alkyl substituted phenol, formaldehyde and polyalkylene polyamine.
U.S. Pat. No. A-4354950 discloses a lubricating oil additive prepared by reacting a hydrocarbyl substituted succinic anhydride with an amino phenol to produce an intermediate N-(hydroxyaryl) hydrocarbyl succinimide. This intermediate is then reacted with an alkylene diamine or polyalkylene polyamine and an aldehyde in a Mannich Base reaction.
U.S. Pat. Nos. A-5219480, A-5128056, and A-5043084 disclose lubricating additives comprising Mannich Base condensates of polymers, an optionally alkylsubstituted N-hydroxyaryl compound, an aldehyde, and an amine, and are incorporated by reference.
U.S. Pat. No. A-5259968 and the divisional thereof, U.S. Pat. No. A-5306313 disclose dispersant additives comprising the reaction product of a Mannich condensation product formed by condensing a long chain hydrocarbyl substituted hydroxyaromatic compound with an aldehyde and polyamine and reacting with a polyanhydride.
U.S. Pat. No. A-5102570 discloses a process for preparing a lubricating oil additive comprising the steps of reacting an amine with an alkenyl suetinit acid anhydride to form a mono- and/or bis-alkenyl succinimide; adding a hydroxyaromatic amine and an excess of formaldehyde to form a Mannich hydroxy aromatic amine coupled mono- and/or bis-alkenyl succinimide; and, acylating with an acylating agent.
Polyalkenyl succinimides are a widely used class of dispersants for lubricant and fuels applications. They are prepared by the reaction of, for example, polyisobutylene with maleic anhydride to form polyisobutenylsuccinic anhydride, and a subsequent condensation reaction with polyethylene amines.
EP-A 0 475 609 A1 discloses the use of"heavy polyamine" which is disclosed to be a mixture of polyethyleneamines sold by Union Carbide Co. under the designation Polyamine HP A-X.
U.S. Pat. No. A-5230714 discloses the use of "polyamine bottoms" derived from an alkylene polyamine mixture. "Polyamine bottoms" are characterized as having less than 2, usually less than 1% by weight of material boiling below about 200.degree. C. In the case of ethylene polyamine bottoms, the bottoms were disclosed to contain less than about 2% by weight total diethylene triamine (DETA) or triethylene tetraamine (TETA). A typical sample of such ethylene polyamine from Dow Chemical Company, designated as "E-100" was disclosed to have a percent nitrogen by weight of 33.15 and gas chromatography analysis showed it to contain about 0.93% "Light Ends" (DETA), 0,72% TETA, 21.74% tetraethylene pentamine and 76.61% pentaethylene hexamine and higher (by weight).
U.S. Pat. No. A-4938881 similarly discloses the use of "polyamine bottoms".
U.S. Pat. No. A-5164101 discloses the polybutenylsuccinimide of polyamines, wherein the polyamine has a specific formula.
U.S. Pat. No. A-5114435 discloses a polyalkylenesuccinimide prepared from a polyalkylenesuccinic acid or anhydride reacted with a polyalkylene polyamine of a specific formula. Hexaethylene heptamine is disclosed to be a suitable amine.
U.S. Pat. No. A-4927551 discloses a polybutenyl succinic anhydride reacted with Dow E-100 heavy polyamine (average Mw=303 available from Dow Chemical Company).
U.S. Pat. No. A-5241003 discloses succinimides derived from amines of a specific formula. Various suitable low cost polyethylene polyamine mixtures are disclosed to be available under various trade designations such as "Polyamine H", "Polyamine 400", "Dow Polyamine E-100" and "Dow S-1107".
U.S. Pat. No. A-4152499 discloses isobutene polymer reacted with maleic anhydride and this adduct then converted into a lubricating oil additive by reaction with polyamines of a specific formula. Diethylenetriamine and triethylenetetramine are disclosed to be suitable amines.
U.S. Pat. No. A-5053 152 and the divisional thereof, U.S. Pat. No. A-5160648, disclose condensates produced by the acid catalyzed condensation of an amine reactant with a hydroxy alkyl or hydroxy aryl reactant. The amine reactant is disclosed to be a high molecular weight extended polyamine.
U.S. Pat. No. A-5171466 discloses dispersants formed by reacting an aliphatic hydrocarbyl substituted succinic acylating agent in which the hydrocarbyl substituent contains an average of at least 40 carbon atoms with a mixture consisting essentially of hydrocarbyl polyamines containing from 10 to 50 weight percent acyclic alkylene polyamines and 50 to 90 weight percent cyclic alkylene polyamines.